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Uncovering the Importance of Proton Donors in TmI 2 ‐Promoted Electron Transfer: Facile CN Bond Cleavage in Unactivated Amides
Author(s) -
Szostak Michal,
Spain Malcolm,
Procter David J.
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201303178
Subject(s) - chemistry , amide , lanthanide , bond cleavage , reagent , cleavage (geology) , nucleophile , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , catalysis , ion , materials science , fracture (geology) , composite material
Nonclassical lanthanide(II) iodides are modern reagents for the development of challenging electron‐transfer processes. It was demonstrated that alcohols are critical for the formation of a thermodynamically more powerful reductant from TmI 2 (thulium diiodide), the first nonclassical lanthanide(II) iodide in the series (TmI 2 , DyI 2 , NdI 2 ). The TmI 2 (ROH) n reagent promotes an unprecedented cleavage of the σ CN bond in amides.